Olefin waxes having improved hardness or viscosity

ABSTRACT

In one embodiment, we disclose hardened olefin waxes and processes for preparing them. In another embodiment, we disclose oxidized olefin waxes having low viscosity and processes for preparing them. The waxes are suitable for use as polishes, coatings, or inks, among other uses. For example, a hardened olefin wax composition produced from a feedstock olefin wax composition by contacting the feedstock olefin wax composition with an oxygen-containing gas at a temperature greater than a melting point of the feedstock olefin wax composition, the hardened olefin wax composition having: a needle penetration value at 25° C. at least 5 percent less than a needle penetration value at 25° C. of the feedstock olefin wax composition; a a kinematic viscosity at 100° C. of up to about 200% greater than the kinematic viscosity of the feedstock olefin wax composition; and a saponification number less than 5 mg KOH/g hardened olefin wax composition.

CROSS REFERENCE TO RELATED APPLICATIONS

The present application is a continuation application of U.S. patentapplication Ser. No. 11/044,794 filed on Jan. 27, 2005, which isentitled “Olefin Waxes Having Improved Hardness or Viscosity” now U.S.Pat. No. 7,527,686 and is a continuation-in-part of U.S. patentapplication Ser. No. 10/996,331 filed Nov. 23, 2004 now U.S. Pat. No.7,341,619. U.S. patent application Ser. No. 10/996,331 is herebyincorporated herein by reference in its entirety for all purposes.

BACKGROUND OF THE INVENTION

The present invention relates generally to the fields of alpha olefinwaxes. More particularly, it concerns alpha olefin wax compositionhaving high hardness, or oxidized alpha olefin wax compositions havinglow viscosity.

Hydrocarbon waxes, such as alpha olefin waxes, paraffin waxes,microcrystalline waxes, polyethylene waxes, and Fisher-Tropsch waxes,are characterized by a set of basic physical property parameters, whichare used to predict or correlate performance in specific applications.The most commonly cited wax physical properties are hardness, dropmelting point, and viscosity. For most wax products, these fundamentalproperties are governed by the molecular weight. As relatively lowmolecular weight waxes, alpha olefin (AO) waxes are relatively soft, buthave desirable high melt flow stemming from their low molecular weight.On the other hand, extremely hard waxes, such as polyethylene waxes,have desirable high physical strength, but their viscosity is usuallyundesirably very high due to their extremely high molecular weights.

For many wax applications, the physical strength, or the hardness ofwaxes, is one of the most important performance criterions inapplications such as polishing (floor, furniture and automobile),coating (textile, fruit, paper), candle formulation, investment casting,and a range of industrial composite structures. It would be desirable toimprove the physical strength of alpha olefin waxes for improvedperformance in current applications or use in applications for whichthey have not yet been suitable. Further, it would be desirable if animprovement in physical strength could be achieved with minimal impacton the low melt viscosity of the alpha olefin waxes. A low meltviscosity is a highly desirable process characteristic for anyhydrocarbon wax to ensure adequate flow during the processing stage inmany applications. A combination of high physical strength and lowviscosity has been difficult to achieve in one wax product as physicalstrength and viscosity both generally have a positive correlation withmolecular weight.

It is well known that a range of hydrocarbon waxes can be oxidized intofunctional waxes by reacting oxygen or oxygen-containing gas with waxesat elevated temperatures. The oxidation changes the chemicalcompositions via a free-radical mechanism, which converts hydrocarbonmolecules of waxes into esters, acids, and other minor components. Theresulting oxidized waxes can be suitable for a range of specificapplications where either high polarity or functionality is required.Many applications require a substantial oxidation of the non-polarhydrocarbon waxes. As a result, many processes have been developed formaximizing the oxidation efficiency for a high level of oxidation. Theseprocesses include use of an autoclave reactor in a batch process, or areaction column or tubular reactor in a continuous process. The typicalsaponification numbers of oxidized waxes can be similar to those ofnatural waxes. For example, the typical saponification numbers ofoxidized waxes are in the range of 50-150 mg KOH/g, and typical acidnumbers are in the range of 30-50 mg KOH/g.

For some specialty applications, oxidized waxes are desirable, asdescribed in U.S. Pat. Nos. 3,901,789; 3,994,737; 4,004,932; 4,180,408;4,240,795; 4,426,229; 6,169,148 and 6,348,547. However, oxidation ofhydrocarbon waxes generally leads to compromised physical properties,such as higher viscosity, as well as discoloration from white toundesirably off-white color.

For a number of applications where an oxidized wax can be useful, itwould be desirable to have an oxidized hydrocarbon wax with bothadequate hardness and relatively low viscosity.

SUMMARY OF THE INVENTION

In one embodiment, the present invention relates to a process to producea hardened olefin wax composition, comprising contacting a feedstockolefin wax composition comprising an olefin having at least 20 carbonatoms with an oxygen-containing gas at a temperature greater than thefeedstock olefin wax composition melting point, to produce a hardenedolefin wax composition, wherein the hardened olefin wax composition hasa needle penetration value at 25° C. at least 5 percent less than theneedle penetration value at 25° C. of the feedstock olefin waxcomposition.

The present invention also relates to the hardened olefin waxcomposition produced by the process.

In one embodiment, the present invention relates to a process to oxidizea feedstock olefin wax composition, comprising (a) contacting afeedstock olefin wax composition comprising an olefin having at least 20carbon atoms with an oxygen-containing gas at a temperature greater thanthat of the feedstock olefin wax composition melting point, to preparean oxidized olefin wax wherein the oxidized olefin wax composition hasan acid number greater than 1 mg KOH/g oxidized olefin wax compositionand a kinematic viscosity at 100° C. less than 70 cSt.

The present invention also relates to the oxidized olefin waxcomposition produced by the process.

The hardened olefin wax compositions generally have hardness at least asgood as or better than the feedstock olefin wax composition. Theoxidized olefin wax compositions generally have relatively lowviscosity.

In another embodiment, the present invention relates to an alpha olefinwax composition, comprising an alpha olefin wax composition comprisingan alpha olefin having at least 20 carbon atoms and at least oneadditive selected from the group consisting of an amide, imide, ormixture thereof, wherein the alpha olefin wax composition has a lowerneedle penetration value at 25° C. than an alpha olefin wax compositionnot comprising the at least one additive.

The hardened olefin wax compositions and the oxidized olefin waxcompositions of the present invention can be used in a variety ofapplications, including, but not limited to, polishes (such as floorwaxes, furniture waxes, or automobile waxes, among others), coatings(such as textile lubricants or controlled release agents, among others),or inks, among others.

DESCRIPTION OF ILLUSTRATIVE EMBODIMENTS

The invention relates to olefin wax compositions and the methods ofmaking the olefin wax compositions. In some embodiments the olefin waxcompositions comprise an additive. In other embodiments the olefin waxcompositions have a hardness greater than the starting olefin waxcomposition. In yet other embodiments the invention relates to oxidizedolefin wax compositions and methods of preparing the oxidized olefin waxcompositions.

Additive-Hardened Wax Compositions

In one embodiment, the invention is an additive-hardened olefin waxcomposition comprising an olefin wax composition and at least oneadditive. The olefin wax composition may be any olefin wax compositionas described herein. Generally, the additive comprises a moiety selectedfrom the group consisting of an amide, imide, or mixture thereof. Insome embodiments, the additive comprises an imide moiety. In yet otherembodiments, the additive comprises an ethylene-bis-amide,ethylene-bis-imide, or mixtures thereof. Independently, in oneembodiment, the additive is a stearamide. In one further embodiment, theadditive is ethylene-bis-stearamide.

The additive-hardened wax composition can comprise any amount of theadditive. In one embodiment, the additive-hardened wax compositioncomprises less than about 10 weight percent of the additive. In afurther embodiment, the additive-hardened wax composition comprises lessthan about 6 weight percent of the additive. In still a furtherembodiment, the additive-hardened wax composition comprises less thanabout 4 weight percent of the additive. In yet a further embodiment, theadditive-hardened wax composition comprises less than about 3 weightpercent of the additive. In an even further embodiment, theadditive-hardened wax composition comprises less than about 2 weightpercent of the additive. In even still a further embodiment, theadditive-hardened wax composition comprises less than about 1 weightpercent of the additive.

Generally, the additive may function to increase the hardness of theadditive-hardened wax composition relative to the olefin waxcomposition. One method that can be used to determine hardness is needlepenetration. Needle penetration can be measured using ASTM D1321 and canbe measured at any acceptable temperature. Unless stated otherwise, theneedle penetrations discussed and presented throughout thisspecification will refer to the needle penetration as measured by ASTMD1321 at 25° C.

In an embodiment, the additive-hardened wax composition can have a lowerneedle penetration value at 25° C. than a reference compositionconsisting of the olefin wax composition. In some embodiments, theadditive may function to reduce the needle penetration of theadditive-hardened wax composition relative to the olefin waxcomposition. In one embodiment, the needle penetration of theadditive-hardened wax composition is at least 5 percent less than theneedle penetration of the olefin wax composition. In another embodiment,the needle penetration of the additive-hardened wax composition is atleast 10 percent less than the needle penetration value of the olefinwax composition. In a further embodiment, the needle penetration of theadditive-hardened wax composition is at least 20 percent less than theneedle penetration value of the olefin wax composition. In still afurther embodiment, the needle penetration of the additive-hardened waxcomposition is at least 30 percent less than the needle penetrationvalue of the olefin wax composition. In yet a further embodiment, theneedle penetration of the additive-hardened wax composition is at least40 percent less than the needle penetration of the olefin waxcomposition. In still a further embodiment, the needle penetration ofthe additive-hardened wax composition is at least 50 percent less thanthe needle penetration value of the olefin wax composition. In generaland as the skilled artisan will be aware, the absolute value of theneedle penetration of the olefin wax composition, and the absolutereduction of the needle penetration as a result of the additive maydepend on the specific composition of the olefin wax composition.

The additive-hardened wax composition may have a higher drop melt pointthan the olefin wax composition. Unless explicitly stated otherwise, alldrop melt points referred to herein are measured according to ASTM D127. In one embodiment, the drop melt point of the additive-hardened waxcomposition is at least 25 percent greater than the drop melt point ofthe olefin wax composition. In a further embodiment, the drop melt pointof the additive-hardened wax composition is at least 50 percent greaterthan the drop melt point of the olefin wax composition. In still afurther embodiment, the drop melt point of the additive-hardened waxcomposition is at least 75 percent greater than the drop melt point ofthe olefin wax composition. In yet a further embodiment, the drop meltpoint of the additive-hardened wax composition is at least 100 percentgreater than the drop melt point of the olefin wax composition.

Hardened Olefin Wax Compositions

In another embodiment, the present invention relates to a hardenedolefin wax composition, produced by a process comprising contacting afeedstock olefin wax composition with an oxygen-containing gas at atemperature greater than the feedstock olefin wax composition meltingpoint. In another embodiment, the present invention relates to ahardened olefin wax composition, produced by a process comprisingcontacting a feedstock olefin wax composition with an oxygen-containinggas at a temperature greater than the feedstock olefin wax compositionmelting point wherein the hardened olefin wax composition has a needlepenetration value at 25° C. at least 5 percent less than the needlepenetration value at 25° C. of the feedstock olefin wax composition. Inanother embodiment, the present invention relates to a hardened olefinwax composition, produced by a process comprising contacting a feedstockolefin wax composition comprising an olefin having at least 20 carbonatoms with an oxygen-containing gas at a temperature greater than thefeedstock olefin wax composition melting point wherein the hardenedolefin wax composition has a needle penetration value at 25° C. at least5 percent less than the needle penetration value at 25° C. of thefeedstock olefin wax composition. Additional process steps and olefinwax product properties that may be used to further describe the hardenedolefin wax composition are described herein. The feedstock olefin waxcompositions which can be used in the process steps are furtherdescribed herein.

The hardened olefin wax composition may also be described usingadditional qualitative and quantitative tests. For example, the hardenedolefin wax composition may be defined by one or more of absolute needlepenetration value, relative needle penetration value, acid number,saponification number, kinematic viscosity, or color, among others. Acidnumber values, when referred to herein, are measured according to ASTM D974, unless explicitly stated to the contrary. All saponificationnumbers described herein are measured by ASTM D94, unless explicitlystated to the contrary. All kinematic viscosities are the 100° C.kinematic viscosities as measured by ASTM D445, unless explicitly statedto the contrary. All ASTM standards referred to herein are the mostcurrent versions as of the filing date of the present application.

Generally, the hardened olefin wax composition has a needle penetrationvalue at 25° C. at least 5 percent less than the needle penetrationvalue at 25° C. of the feedstock olefin wax composition. In oneembodiment, the hardened olefin wax composition has a needle penetrationat least 10 percent less than the needle penetration of the feedstockolefin wax composition. In a further embodiment, the hardened olefin waxcomposition has a needle penetration at least 20 percent less than theneedle penetration of the feedstock olefin wax composition. In still afurther embodiment, the hardened olefin wax composition has a needlepenetration at least 30 percent less than the needle penetration of thefeedstock olefin wax composition. In yet a further embodiment, thehardened olefin wax composition has a needle penetration at least 40percent less than the needle penetration of the feedstock olefin waxcomposition. In still a further embodiment, the hardened olefin waxcomposition has a needle penetration at least 50 percent less than theneedle penetration of the feedstock olefin wax composition.

Quantitatively, the hardened olefin wax composition can have an acidnumber of less than about 12 mg KOH/g hardened olefin wax composition.In one embodiment, the hardened olefin wax composition can have an acidnumber less than about 10 mg KOH/g hardened olefin wax composition. In afurther embodiment, the hardened olefin wax composition can have an acidnumber less than about 5 mg KOH/g hardened olefin wax composition. Instill a further embodiment, the hardened olefin wax composition can havean acid number less than about 2 mg KOH/g hardened olefin waxcomposition. In yet a further embodiment, the hardened olefin waxcomposition can have an acid number less than about 1 mg KOH/g hardenedolefin wax composition.

Also quantitatively, the hardened olefin wax composition can have asaponification number of less than about 45 mg KOH/g hardened olefin waxcomposition. In one further embodiment, the hardened olefin waxcomposition has a saponification number less than about 25 mg KOH/ghardened olefin wax composition. In still a further embodiment, thehardened olefin wax composition has a saponification number less thanabout 15 mg KOH/g hardened olefin wax composition. In yet a furtherembodiment, the hardened olefin wax composition has a saponificationnumber less than about 10 mg KOH/g hardened olefin wax composition. Ineven a further embodiment, the hardened olefin wax composition has asaponification number less than about 5 mg KOH/g hardened olefin waxcomposition. In another embodiment, the hardened olefin wax compositionhas a saponification number less than about 2.5 mg KOH/g hardened olefinwax composition.

Also quantitatively, the hardened olefin wax composition can have akinematic viscosity up to about 500% greater than the kinematicviscosity of the feedstock olefin wax composition. In one furtherembodiment, the hardened olefin wax composition has a kinematicviscosity up to about 300% greater than the kinematic viscosity of thefeedstock olefin wax composition. In still a further embodiment, thehardened olefin wax composition has a kinematic viscosity up to about200% greater than the kinematic viscosity of the feedstock olefin waxcomposition. In yet a further embodiment, the hardened olefin waxcomposition has a kinematic viscosity up to about 150% greater than thekinematic viscosity of the feedstock olefin wax composition. In even afurther embodiment, the hardened olefin wax composition has a kinematicviscosity up to about 100% greater than the kinematic viscosity of thefeedstock olefin wax composition. In even still a further embodiment,the hardened olefin wax composition has a kinematic viscosity that issubstantially unchanged relative to the kinematic viscosity of thefeedstock olefin wax composition. By “substantially unchanged kinematicviscosity” is meant the kinematic viscosity is up to about 30% greaterthan the kinematic viscosity of the feedstock olefin wax composition.

Also quantitatively, the hardened olefin wax composition can have a dropmelt point substantially unchanged relative to the drop melt point ofthe feedstock olefin wax composition. By “substantially unchanged dropmelt point” is meant the drop melt point of the hardened olefin waxcomposition is from about 10% less than the drop melt point of thefeedstock olefin wax composition to about 10% greater than the drop meltpoint of the feedstock olefin wax composition.

Qualitatively, the hardened olefin wax composition generally retains itswhite color. However, the invention encompasses hardened olefin waxcomposition colors ranging from white to light yellow.

Though the process of preparing the hardened olefin wax compositionhaving a reduced needle penetration relative to the feedstock olefin waxcomposition involves contacting the feedstock olefin wax compositionwith an oxygen-containing gas, it has been discovered that conditionsused to produce the hardened olefin wax composition described herein donot always significantly oxidize the olefin wax composition.Specifically, the low acid numbers and low saponification numbersobserved for some embodiments of the hardened olefin wax compositionindicate that a significant portion of the feedstock olefin waxcomposition is not oxidized. Thus, the hardened olefin wax compositionmay alternatively be described in terms of physical properties of thefeedstock olefin wax composition which do not change significantly as aresult of the oxygen-containing gas contact step in combination withproperties of the hardened olefin wax composition properties whichdiffer significantly from the properties of the feedstock olefin waxcomposition as a result of the oxygen-containing gas contact step.Examples of the feedstock olefin wax composition properties which do notchange significantly as a result of the oxygen-containing gas contactstep and which may be used either singly or in combination to describethe hardened olefin wax composition include feedstock olefin waxcomposition average molecular weight, average olefin molecular weight,feedstock olefin wax composition carbon number composition, or feedstockolefin wax olefin composition, among others. Examples of the hardenedolefin wax composition properties which may differ measurably from theproperties of the feedstock olefin wax composition as a result of theoxygen-containing gas contact step and which may be used either singlyor in any combination to describe the hardened olefin wax compositioninclude needle penetration, viscosity, drop melt point, acid number, andsaponification number, among others. Thus, a combination of thefeedstock olefin wax composition properties that do not changesignificantly due to contact with the oxygen-containing gas contact stepand properties which may differ measurably due to contact with theoxygen-containing gas may be used to describe the hardened olefin waxcomposition. For example, in one non-limiting exemplary hardened olefinwax composition, the hardened olefin wax composition has an averagemolecular weight substantially the same as the feedstock olefin waxcomposition and a needle penetration 5 percent less than the needlepenetration of the feedstock olefin wax composition. In a secondnon-limiting example of a hardened olefin wax composition, the hardenedolefin wax composition comprises an olefin wax having an average olefinmolecular weight from 260 grams/mole to 340 grams/mole and a needlepenetration 30 percent less than the needle penetration of the feedstockolefin wax composition.

In one embodiment, the present invention relates to a hardened olefinwax composition having an average olefin molecular weight between 260grams/mole and 340 grams/mole and a needle penetration value less than100 dmm. When referring to hardened olefin wax compositions, the term“average olefin molecular weight” refers to the average molecular weightfor all olefins in the hardened olefin wax composition. In otherembodiments, the hardened olefin wax composition having an averageolefin molecular weight between 260 grams/mole and 340 grams/mole has aneedle penetration less than 90 dmm, alternatively less than 80 dmm,alternatively less than 70 dmm, and alternatively less than 60 dmm.

In another embodiment, the hardened olefin wax composition has anaverage olefin molecular weight between 280 grams/mole and 320grams/mole and a needle penetration value less than 100 dmm. In otherembodiments, the hardened olefin wax composition having an averageolefin molecular weight between 280 grams/mole and 320 grams/mole has aneedle penetration less than 90 dmm, alternatively less than 80 dmm,alternatively less than 70 dmm, and alternatively less than 60 dmm.

In another embodiment, the hardened olefin wax composition has anaverage olefin molecular weight between 290 grams/mole and 310grams/mole and a needle penetration value less than 100 dmm. In otherembodiments, the hardened olefin wax composition having an averageolefin molecular weight between 290 grams/mole and 310 grams/mole has aneedle penetration less than 90 dmm, alternatively less than 80 dmm,alternatively less than 70 dmm, and alternatively less than 60 dmm.

The hardened olefin wax composition may also have an acid number,saponification number, color or combination of these as described above.

In one embodiment, the present invention relates to a hardened olefinwax composition having an average olefin molecular weight between 330grams/mole and 420 grams/mole and a needle penetration value less than35 dmm. In other embodiments, the hardened olefin wax composition havingan average olefin molecular weight between 330 grams/mole and 420grams/mole has a needle penetration less than 30 dmm, alternatively lessthan 25 dmm, and alternatively less than 20 dmm.

In another embodiment, the hardened olefin wax composition has anaverage olefin molecular weight between 350 grams/mole and 400grams/mole and a needle penetration value less than 35 dmm. In otherembodiments, the hardened olefin wax composition having an averageolefin molecular weight between 350 grams/mole and 400 grams/mole has aneedle penetration less than 30 dmm, alternatively less than 25 dmm, andalternatively less than 20 dmm.

In another further embodiment, the hardened olefin wax composition hasan average olefin molecular weight between 360 grams/mole and 390grams/mole and a needle penetration value less than 35 dmm. In otherembodiments, the hardened olefin wax composition having an averageolefin molecular weight between 360 grams/mole and 390 grams/mole has aneedle penetration less than 30 dmm, alternatively less than 25 dmm, andalternatively less than 20 dmm.

Independently, the hardened olefin wax composition having an averageolefin molecular weight between 330 grams/mole and 420 grams per molecan have a kinematic viscosity between about 3 cSt and about 15 cSt; ina further embodiment, between about 3.5 cSt and about 12 cSt; in still afurther embodiment, between about 3.5 cSt and about 8 cSt; in yet afurther embodiment, between about 3.75 cSt and about 6 cSt.Independently, the hardened olefin wax composition having an averageolefin molecular weight between 350 grams/mole and 400 grams per molecan have a kinematic viscosity between about 3 cSt and about 15 cSt; ina further embodiment, between about 3.5 cSt and about 12 cSt; in still afurther embodiment, between about 3.5 cSt and about 8 cSt; in yet afurther embodiment, between about 3.75 cSt and about 6 cSt.Independently, the hardened olefin wax composition having an averageolefin molecular weight between 360 grams/mole and 390 grams per molecan have a kinematic viscosity between about 3 cSt and about 15 cSt; ina further embodiment, between about 3.5 cSt and about 12 cSt; in still afurther embodiment, between about 3.5 cSt and about 8 cSt; in yet afurther embodiment, between about 3.75 cSt and about 6 cSt.Independently, the hardened olefin wax composition having an averageolefin molecular weight between 330 grams/mole and 420 grams per mole,alternatively between 350 grams/mole and 400 grams/mole, andalternatively between 360 grams/mole and 390 grams/mole can have a dropmelt point between about 50° C. and about 70° C. The hardened olefin waxcomposition may also have an acid number, saponification number, coloror any combination of these as described above.

In one embodiment, the present invention relates to a hardened olefinwax composition having an average olefin molecular weight between 440grams/mole and 550 grams/mole and a needle penetration value less than10 dmm. In other embodiments, the hardened olefin wax composition havingan average olefin molecular weight between 440 grams/mole and 550grams/mole has a needle penetration less than 9 dmm, alternatively lessthan 7 dmm, and alternatively less than 5 dmm.

In another embodiment, the hardened olefin wax composition has anaverage olefin molecular weight between 460 grams/mole and 530grams/mole and a needle penetration value less than 10 dmm. In otherembodiments, the hardened olefin wax composition having an averageolefin molecular weight between 460 grams/mole and 530 grams/mole has aneedle penetration less than 9 dmm, alternatively less than 7 dmm, andalternatively less than 5 dmm.

In another embodiment, the hardened olefin wax composition has anaverage olefin molecular weight between 480 grams/mole and 510grams/mole and a needle penetration value less than 10 dmm. In otherembodiments, the hardened olefin wax composition having an averageolefin molecular weight between 480 grams/mole and 510 grams/mole has aneedle penetration less than 9 dmm, alternatively less than 7 dmm, andalternatively less than 5 dmm.

Independently, the hardened olefin wax composition having an averageolefin molecular weight between 440 grams/mole and 550 grams per molecan have a kinematic viscosity between about 7 cSt and about 35 cSt,alternatively between about 7.5 cSt and about 30 cSt; in still a furtherembodiment, between about 7.5 cSt and about 25 cSt; in yet a furtherembodiment, between about 8 cSt and about 14 cSt. Independently, thehardened olefin wax composition having an average olefin molecularweight between 460 grams/mole and 530 grams per mole can have akinematic viscosity between about 7 cSt and about 35 cSt, alternativelybetween about 7.5 cSt and about 30 cSt; in still a further embodiment,between about 7.5 cSt and about 25 cSt; in yet a further embodiment,between about 8 cSt and about 14 cSt. Independently, the hardened olefinwax composition having an average olefin molecular weight between 480grams/mole and 510 grams per mole can have a kinematic viscosity betweenabout 7 cSt and about 35 cSt, alternatively between about 7.5 cSt andabout 30 cSt; in still a further embodiment, between about 7.5 cSt andabout 25 cSt; in yet a further embodiment, between about 8 cSt and about14 cSt. Independently, the hardened olefin wax composition having anaverage olefin molecular weight between 440 grams/mole and 550 grams permole, alternatively between 460 grams/mole and 530 grams per mole, andalternatively between 480 grams/mole and 510 grams per mole may have adrop melt point between about 60° C. and about 80° C. The hardenedolefin wax composition may also have an acid number, saponificationnumber, color or any combination of these as described above.

The hardened olefin wax composition of any of the immediately foregoingembodiments can be non-oxidized, as quantified by an acid number lessthan 12 mg KOH/g hardened olefin wax composition or a saponificationnumber less than 45 mg KOH/g hardened olefin wax composition, asdescribed above. The hardened olefin wax composition of any of theimmediately foregoing embodiments can comprise predominately any olefinwax composition described herein. In a non-limiting example, thehardened olefin wax composition can comprise an alpha olefin. Further,the hardened olefin wax composition can have an alpha olefin contentgreater than 50 mole percent. In a further embodiment, the hardenedolefin wax composition has an alpha olefin content greater than 70 molepercent. In still a further embodiment, the hardened olefin waxcomposition has an alpha olefin content greater than 80 mole percent. Inyet a further embodiment, the hardened olefin wax composition has analpha olefin content greater than 90 mole percent.

A hardened olefin wax composition described herein can be used as acomponent of a polish, coating, candle, paint, ink, hot melt adhesive,investment casting composition, wood additive composition, or waxemulsion. In particular embodiments, the hardened olefin waxcompositions can be used as polishes (such as floor waxes, furniturewaxes, or automobile waxes, among others), coatings (such as textilelubricants or controlled release agents, among others), or inks, amongothers. These lists of uses are neither exhaustive nor limiting.

Oxidized Olefin Wax Compositions

Generally, another aspect of the present invention relates to anoxidized olefin wax composition, produced by a process comprisingcontacting a feedstock olefin wax composition with an oxygen-containinggas at a temperature greater than the melting point of the feedstockolefin wax composition. In an additional embodiment, the presentinvention relates to an oxidized olefin wax composition, produced by aprocess comprising contacting a feedstock olefin wax composition with anoxygen-containing gas at a temperature greater than the melting point ofthe feedstock olefin wax composition, wherein the oxidized olefin waxhas an acid number greater than 1 mg KOH/g oxidized olefin waxcomposition and a kinematic viscosity, at 100° C., less than 70 cSt. Inan additional embodiment, the present invention relates to an oxidizedolefin wax composition, produced by a process comprising contacting afeedstock olefin wax composition comprising an olefin having at least 20carbon atoms with an oxygen-containing gas at a temperature greater thanthe melting point of the feedstock olefin wax composition, wherein theoxidized olefin wax has an acid number greater than 1 mg KOH/g oxidizedolefin wax composition and a kinematic viscosity, at 100° C., less than70 cSt. Additional process steps and oxidized olefin wax compositionparameters that further describe the invention are provided herein.Additional properties that describe the feedstock olefin wax subject tothe oxidation process steps are also provided herein.

In an embodiment, the acid number of the oxidized olefin wax compositionis greater than 1 mg KOH/g oxidized olefin wax composition. In anotherembodiment, the acid number of the oxidized olefin wax composition canbe between 1 mg KOH/g oxidized olefin wax composition and 200 mg KOH/goxidized olefin wax composition. In a further embodiment, the acidnumber can be between 2 mg KOH/g oxidized olefin wax composition and 100mg KOH/g oxidized olefin wax composition. In still a further embodiment,the acid number can be between 4 mg KOH/g oxidized olefin waxcomposition and 50 mg KOH/g oxidized olefin wax composition.

In an embodiment, the kinematic viscosity, at 100° C., of the oxidizedolefin wax composition can be less than 70 cSt. In another embodiment,the kinematic viscosity, at 100° C., of the oxidized olefin waxcomposition can be between 2 cSt and 70 cSt. In a further embodiment,the kinematic viscosity, at 100° C., of the oxidized olefin waxcomposition can be between 3 cSt and 50 cSt. In still a furtherembodiment, the kinematic viscosity, at 100° C., of the oxidized olefinwax composition can be between 5 cSt and 25 cSt.

In one embodiment, the oxidized olefin wax composition has a needlepenetration value between 400 percent greater than and 75 percent lessthan the needle penetration value of the feedstock olefin waxcomposition. In a further embodiment, the oxidized olefin waxcomposition has a needle penetration from about 0 percent greater toabout 400 percent greater than the needle penetration of the feedstockolefin wax composition. In yet a further embodiment, the oxidized olefinwax composition has a needle penetration from about 0 percent greater toabout 300 percent greater than the needle penetration of the feedstockolefin wax composition. In still a further embodiment, the oxidizedolefin wax composition has a needle penetration from about 0 percentgreater to about 200 percent greater than the needle penetration of thefeedstock olefin wax composition. In even a further embodiment, theoxidized olefin wax composition has a needle penetration from about 0percent greater to about 100 percent greater than the needle penetrationof the feedstock olefin wax composition.

Independently, in a further embodiment, the oxidized olefin waxcomposition can have a needle penetration value at least 5% less thanthe needle penetration value of the feedstock olefin wax. In yet afurther embodiment, the oxidized olefin wax composition can have aneedle penetration value at least 10% less than the needle penetrationvalue of the feedstock olefin wax composition. In still a furtherembodiment, the oxidized olefin wax composition can have a needlepenetration value at least 20% less than the needle penetration value ofthe feedstock olefin wax composition. In even a further embodiment, theoxidized olefin wax composition can have a needle penetration value atleast 30% less than the needle penetration value of the feedstock olefinwax composition. In even yet a further embodiment, the oxidized olefinwax composition can have a needle penetration value at least 40% lessthan the needle penetration value of the feedstock olefin waxcomposition. In even still a further embodiment, the oxidized olefin waxcomposition can have a needle penetration value at least 50% less thanthe needle penetration value of the feedstock olefin wax composition.

In one embodiment, the oxidized olefin wax composition has a drop meltpoint that is substantially unchanged from that of the feedstock olefinwax composition.

The oxidized olefin wax compositions of the present invention can beused in applications similar to those described above. In light of thepresent disclosure of the properties of the olefin wax compositions,additive-hardened olefin wax compositions, and hardened olefin waxcompositions, and oxidized olefin wax compositions of the presentinvention, the skilled artisan can routinely determine which wax may besuitable or desirable for a particular use.

Hardened Olefin Wax Compositions—Method for Producing

Generally, the hardened olefin wax compositions are produced bycontacting a feedstock olefin wax composition with an oxygen-containinggas. Additional process parameters which may be used to define theprocess to produce the hardened olefin wax compositions may include theoxygen content of the oxygen-containing gas, the temperature at whichthe feedstock olefin wax composition and oxygen-containing gas arecontacted, the time for which the oxygen-containing gas and thefeedstock olefin wax composition are contacted, and whether or not thefeedstock olefin wax composition is mixed, stirred, or agitated duringcontact with the oxygen-containing gas. The independently variableprocess parameters and hardened olefin wax composition propertiesprovided herein may be used to further describe the processes andcompositions of the invention.

In one embodiment, the present invention relates to a process to producea hardened olefin wax composition comprising contacting a feedstockolefin wax composition comprising an olefin having at least 20 carbonatoms with an oxygen-containing gas at a temperature greater than thefeedstock olefin wax composition melting point. In another embodiment,the present invention relates to a process to produce a hardened olefinwax composition, comprising contacting a feedstock olefin waxcomposition comprising an olefin having at least 20 carbon atoms with anoxygen-containing gas at a temperature greater than the feedstock olefinwax composition melting point, to produce a hardened olefin waxcomposition, wherein the hardened olefin wax composition has a needlepenetration value at 25° C. at least 5 percent less than the needlepenetration value at 25° C. of the feedstock olefin wax composition. Thedescription of the feedstock olefin wax composition and hardened olefinwax composition are described herein and are generally applicable to theprocess of producing the hardened olefin wax compositions of thisembodiment. Details regarding the contacting step and process conditionsthat are generally applicable to the process of producing the hardenedolefin wax composition are described below.

The oxygen-containing gas may be any gas containing oxygen. Theoxygen-containing gas can be pure oxygen, oxygen diluted with an inertgas, air, or air diluted with an inert gas, among others. Nitrogen andnoble gases may be referred to herein as “inert gases.” Exemplarymixtures of oxygen diluted with an inert gas or gases include, but arenot limited to, mixtures of oxygen and nitrogen, mixtures of oxygen andargon, mixtures of oxygen and other noble gases, or mixtures of oxygen,nitrogen, and argon, among others. In one embodiment, all gases otherthan oxygen in the mixture are selected from nitrogen or noble gases.

In one embodiment, the oxygen-containing gas can comprise less than 50percent oxygen. In a further embodiment, the oxygen-containing gas cancomprise less than 22 percent oxygen. In another embodiment, theoxygen-containing gas is air.

The contacting of the feedstock olefin wax composition and theoxygen-containing gas can involve any technique known to the skilledartisan. Such techniques can include, but are not limited to, spargingthe gas through the melted feedstock olefin wax composition (with orwithout mixing, stirring, or other agitation of the melted wax) orproviding the gas to the surface of the melted wax with or withoutmixing, stirring, or other agitation of the melted feedstock olefin waxcomposition, among others.

The contacting step can be conducted at any air flow rate and durationcapable of producing the hardened olefin wax compositions describedherein.

In an embodiment, the contacting step for producing the hardened olefinwax composition comprises contacting air with the feedstock olefin waxcomposition at an air flow rate greater than 0.1 CFH/kg feedstock olefinwax composition. In a further embodiment, the air flow rate is between0.1 CFH/kg feedstock olefin wax composition and 15 CFH/kg feedstockolefin wax composition. In a further embodiment, the air flow rate isbetween 0.25 CFH/kg feedstock olefin wax composition and 15 CFH/kgfeedstock olefin wax composition. In a further embodiment, the air flowrate is between 0.5 CFH/kg feedstock olefin wax composition and 10CFH/kg feedstock olefin wax composition. In a further embodiment, theair flow rate is between 0.75 CFH/kg feedstock olefin wax compositionand 8 CFH/kg feedstock olefin wax composition. In a further embodiment,the air flow rate is between 1.0 CFH/kg feedstock olefin wax compositionand 5 CFH/kg feedstock olefin wax composition.

In an embodiment, the contacting step for producing the hardened olefinwax composition can have a duration greater than about 1 minute. In afurther embodiment, the contacting step can have a duration betweenabout 1 minute and 12 hours. In a further embodiment, the contactingstep can have a duration between about 1 minute and 8 hours. In afurther embodiment, the contacting step can have a duration betweenabout 1 minute and 4 hours. In a further embodiment, the contacting stepcan have a duration between about 1 minute and 2 hours. In a furtherembodiment, the contacting step can have a duration between about 1minute and 1 hour.

In other embodiments, the melted feedstock olefin wax composition andthe oxygen-containing gas can be mixed, stirred, or agitated to increasethe intimacy of contact therebetween.

In a separate embodiment, the contacting step for producing the hardenedolefin wax composition is conducted at low air flows. In one low airflow embodiment, the contacting step for producing the hardened olefinwax composition comprises contacting air with the feedstock olefin waxcomposition at an air flow rate less than 0.1 cubic feet per hour(CFH)/kg feedstock olefin wax composition and without substantialagitation of the feedstock olefin wax composition. In this low airflowembodiment, the contacting step can have a duration greater than about 1day. In a further embodiment, the contacting step can have a durationbetween about 1 day and about 60 days. In a further embodiment, thecontacting step can have a duration between about 2 days and about 45days. In a further embodiment, the contacting step can have a durationbetween about 3 days and about 30 days.

The contacting step for producing the hardened olefin wax compositioncan be conducted at a temperature greater than the feedstock olefin waxcomposition melting point. In one embodiment, the feedstock olefin waxcomposition and the oxygen-containing gas are contacted at a temperaturebetween the melting point of the feedstock olefin wax composition and300° C. In a further embodiment, the feedstock olefin wax compositionand the oxygen-containing gas are contacted at a temperature betweenabout 80° C. and 300° C. In a further embodiment, the feedstock olefinwax composition and the oxygen-containing gas are contacted at atemperature between about 100° C. and 250° C. In a further embodiment,the feedstock olefin wax composition and the oxygen-containing gas arecontacted at a temperature between about 180° C. and 230° C. In afurther embodiment, the feedstock olefin wax composition and theoxygen-containing gas are contacted at a temperature between about 200°C. and 220° C.

The contacting step can be performed in the presence or absence of acatalyst. In some embodiments the contacting step is performed in theabsence of an added catalyst. In other embodiments, the contacting stepcan be performed in the presence of a catalyst. In the catalyticembodiment the catalyst may comprise manganese or cobalt, among others.

This process is generally capable of producing a hardened olefin waxcomposition having a having a needle penetration lower than that of thefeedstock olefin wax composition. Additionally, the hardened olefin waxcomposition can have additional properties selected from the groupconsisting of low acid numbers, low saponification numbers,substantially unchanged to slightly higher relative kinematicviscosities, and substantially unchanged relative drop melt points, andcombinations thereof as described herein.

After production of the hardened olefin wax composition, the process canfurther comprise storing the hardened olefin wax composition under aninert gas (i.e., nitrogen, a noble gas, or a mixture thereof). In oneembodiment, the inert gas is nitrogen.

After production of the hardened olefin wax composition, the process canfurther comprise combining the hardened olefin wax composition with atleast one antioxidant. Exemplary antioxidants include, but are notlimited to, 2,6-di(t-butyl)-4-methylphenol (BHT), BHT derivatives,alkylated diphenylamine, alkylated diphenylamine derivatives,N-Phenyl-1-naphthylamine, N-Phenyl-1-naphthylamine derivatives,1,2,3,4,-tetrahydroxybenzene (THB), Irganox 1010, and Irganox 1076. Theantioxidant can be incorporated into the hardened olefin wax compositionat a concentration from about 25 ppm to about 2,500 ppm.

Oxidized Olefin Wax Compositions—Method for Producing

Generally, the oxidized olefin wax compositions are produced bycontacting a feedstock olefin wax composition with an oxygen-containinggas. Additional process parameters which may be used to define theprocess to produce the oxidized olefin wax compositions may include theoxygen content of the oxygen-containing gas, the temperature at whichthe feedstock olefin wax composition and oxygen-containing gas arecontacted, the time for which the oxygen-containing gas and thefeedstock olefin wax composition are contacted, and whether or not thefeedstock olefin wax composition is mixed, stirred, or agitated duringcontact with the oxygen-containing gas. These independently variableprocess parameters are further described herein.

In one embodiment, the present invention relates to a process to oxidizean olefin wax composition, comprising contacting a feedstock olefin waxcomposition comprising an olefin having at least 20 carbon atoms with anoxygen-containing gas at a temperature greater than that of thefeedstock olefin wax composition melting point. In another embodiment,the present invention relates to a process to oxidize an olefin waxcomposition, comprising contacting a feedstock olefin wax compositioncomprising an olefin having at least 20 carbon atoms with anoxygen-containing gas at a temperature greater than that of thefeedstock olefin wax composition melting point, to prepare an oxidizedolefin wax composition wherein the oxidized olefin wax composition hasan acid number greater than 1 mg KOH/g oxidized olefin wax compositionand a kinematic viscosity at 100° C. less than 70 cSt. The feedstockolefin wax composition and oxidized olefin wax composition propertiesare described herein and are generally applicable to the process toproduce the oxidized olefin wax compositions. Process parameters such asthe applicable oxygen-containing gases, contact modes (agitationmethods), and presence or absence of catalyst are generally similar asthose discuses in the process for producing the hardened olefin waxes.However, the contacting step temperature and airflow rates for theprocess to produce the oxidized olefin wax compositions differ from thecontacting step temperature and airflow rates to produce the hardenedolefin wax compositions, and those differences are set forth below.

The temperature of the contacting step to produce the oxidized olefinwax composition can be between the feedstock olefin wax compositionmelting point and 300° C. In a further embodiment, the contacting stepcan be performed at a temperature between about 80° C. and about 300° C.In a further embodiment, the contacting step can be performed at atemperature between about 80° C. and about 200° C. In a furtherembodiment, the contacting step can be performed at a temperaturebetween about 90° C. and about 180° C. In a further embodiment, thecontacting step can be performed at a temperature between about 100° C.and about 160° C. In a further embodiment, the contacting step can beperformed at a temperature between about 110° C. and about 150° C.

In another embodiment, the contacting step for producing the oxidizedolefin wax composition comprises contacting air with the feedstockolefin wax composition at an air flow rate greater than 0.1 CFH/kgfeedstock olefin wax composition. In a further embodiment, the air flowrate is between 0.1 CFH/kg feedstock olefin wax composition and 30CFH/kg feedstock olefin wax composition. In a further embodiment, theair flow rate is between 0.5 CFH/kg feedstock olefin wax composition and20 CFH/kg feedstock olefin wax composition. In a further embodiment, theair flow rate is between 1.0 CFH/kg feedstock olefin wax composition and15 CFH/kg feedstock olefin wax composition. In a further embodiment, theair flow rate is between 1.5 CFH/kg feedstock olefin wax composition and12 CFH/kg feedstock olefin wax. In a further embodiment, the air flowrate is between 2 CFH/kg feedstock olefin wax composition and 10 CFH/kgfeedstock olefin wax composition.

In an embodiment, the contacting step for the process for producing anoxidized olefin wax composition can have a duration between 1 minute and48 hours. In a further embodiment, the duration is between 2 hours and30 hours. In a further embodiment, the duration is between 4 hours and24 hours.

In a separate embodiment, the contacting step for producing the oxidizedolefin wax composition is performed at a low air flow. In this low flowembodiment, the contacting step comprises contacting air with thefeedstock olefin wax composition at an air flow rate less than 0.1CFH/kg feedstock olefin wax composition and without substantialagitation of the feedstock olefin wax composition. In this embodiment,the duration of the contacting step can be greater than 1 day.

The contacting step yields an oxidized olefin wax composition, which mayfurther comprise other compounds, such as volatile compounds. In oneembodiment, the process can further comprise removing volatile compoundsfrom the oxidized olefin wax composition by one or more of vacuum, heat,nitrogen sparging, or contacting with activated charcoal, clay, alumina,or two or more thereof.

Specifically, the oxidized olefin wax composition can be devolatilizedby transfer to an appropriate vessel and connecting the vessel to avacuum apparatus, such as a Kugelrohr rotovap apparatus consisting anair oven, a vacuum pump, and a rotating mechanism to effect a thin filmevaporation function (manufactured by Barnstead International anddistributed by Aldrich, Model No. Z40-115-3). The volatiles can bestripped off by a combination of vacuum (less than 5 mmHg) and heat,such as maintaining the oven temperature from about 140° C. to about220° C. for a duration from about 1 hr to about 12 hr, such as 3 hr.

In one embodiment, the oxidized olefin wax composition may bedevolatilized by applying a vacuum to a vessel comprising the oxidizedolefin wax composition. In another embodiment, the oxidized olefin waxcomposition may be devolatilized by applying a vacuum and heat to avessel comprising the oxidized olefin wax composition. In still anotherembodiment, the oxidized olefin wax composition is mixed, stirred, oragitated during the vacuum devolatilization step. In yet anotherembodiment, a sparging gas is passed through the oxidized olefin waxcomposition during the vacuum devolatilization step. The sparging gascan be an inert gas such as nitrogen, argon, or combinations thereof. Inyet another embodiment, the vacuum devolatilization step may beperformed using a wiped film evaporator. Two or more of heat, agitation,sparging, and wiped film evaporation can be applied during vacuumdevolatilization.

The oxidized olefin wax composition has been described above. The acidnumber and kinematic viscosity of the oxidized olefin wax compositioncan be as described above.

The Feedstock Olefin Wax

The terms olefin wax composition and feedstock olefin wax compositionmay be used interchangeably to describe the compositions subject to theinventions described herein. Generally, the term olefin wax compositionis used when the composition is physically mixed with another material,for example an additive, while the term feedstock olefin wax compositionis used when the composition is the subject of a process, for examplecontact with an oxygen-containing gas. Thus, the olefin wax compositionsdescribed herein also describe the feedstock olefin compositiondescribed herein unless explicitly described otherwise.

The olefin wax composition or the feedstock olefin wax composition canbe any composition comprising an olefin having at least 20 carbon atoms.Generally, an olefin is a hydrocarbon with at least one carbon-carbondouble bond. In some embodiments, the olefin wax composition comprisesan alpha olefin. An alpha olefin is a hydrocarbon with a carbon-carbondouble bond at the terminal position. In other embodiments the olefinwax composition comprises an internal olefin. In other embodiments theolefin wax composition comprises linear internal olefins. In yet otherembodiments the olefin wax composition comprises a normal alpha olefin.A normal alpha olefin is an alpha olefin having a straight chain ofcarbon atoms (i.e. no carbon chain branches) and a carbon-carbon doublebond at the terminal position. Additional criteria which may beindependently applied, either singly or in any combination, to theolefin wax include the olefin wax composition's average olefin molecularweight, olefin wax composition carbon number composition, alpha olefincontent, internal olefin content, linear internal olefin content,vinylidene olefin content, needle penetration, drop melt point, andviscosity, among others, are discussed below.

The olefin wax or feedstock olefin wax may comprise one or more olefins,as described above. In one embodiment, the olefin wax composition orfeedstock olefin wax composition comprises greater than 30 mole %olefins having at least 20 carbon atoms. In a further embodiment, theolefin wax composition comprises greater than 45 mole % olefins havingat least 20 carbon atoms. In yet a further embodiment, the olefin waxcomposition comprises greater than 60 mole % olefins having at least 20carbon atoms. In still a further embodiment, the olefin wax compositioncomprises greater than 75 mole % olefins having at least 20 carbonatoms. In even a further embodiment, the olefin wax compositioncomprises greater than 90 mole % olefins having at least 20 carbonatoms. In even still a further embodiment, the olefin wax compositioncomprises greater than 95 mole % olefins having at least 20 carbonatoms. In yet another embodiment, the olefin wax composition consistsessentially of olefin having at least 20 carbon atoms.

The olefin wax composition or feedstock olefin wax composition mole %olefin compositions are not limited to olefins having at least 20 carbonatoms. The olefin mole % values of the compositions may also be appliedto the olefin wax composition and feedstock olefin wax compositionembodiments having the olefin carbon number compositions and/or theaverage olefin molecular weight ranges as described herein.

In some embodiments, the components of the olefin wax composition orfeedstock olefin wax composition contains a paraffin wax in addition tothe olefin wax. In further embodiments, the olefin wax composition maycontain a paraffin wax having greater than 20 carbon atoms. In yetfurther embodiments, the olefin wax composition contains less than 65mole % paraffins having greater than 20 carbon atoms; alternatively, 50mole % paraffins having greater than 20 carbon atoms; alternatively, 35mole % paraffins having greater than 20 carbon atoms; alternatively, 20mole % paraffins having greater than 20 carbon atoms; alternatively, 8mole % paraffins having greater than 20 carbon atoms; and alternatively,5 mole % paraffins having greater than 20 carbon atoms.

The olefin wax composition or feedstock olefin wax composition mole %paraffin contents are not limited to olefins having at least 20 carbonatoms. The paraffin mole % values of the compositions may also beapplied to same carbon number compositions and/or the average molecularweight ranges as the olefin carbon number compositions and/or theaverage olefin molecular weight ranges described herein.

In some embodiments, the olefin wax composition or feedstock olefin waxcomposition comprises alpha olefins. In one embodiment, the olefin waxcomposition comprises greater than 30 mole % alpha olefins having atleast 20 carbon atoms. In a further embodiment, the olefin waxcomposition comprises greater than 45 mole % alpha olefins having atleast 20 carbon atoms. In yet a further embodiment, the olefin waxcomposition comprises greater than 60 mole % alpha olefins having atleast 20 carbon atoms. In still a further embodiment, the olefin waxcomposition comprises greater than 75 mole % alpha olefins having atleast 20 carbon atoms. In even a further embodiment, the olefin waxcomposition comprises greater than 90 mole % alpha olefins having atleast 20 carbon atoms. In even still a further embodiment, the olefinwax composition comprises greater than 95 mole % alpha olefins having atleast 20 carbon atoms.

The olefin wax composition or feedstock olefin composition wax alphaolefin compositions are not limited to olefins having at least 20 carbonatoms. The alpha olefin mole % values of the compositions may also beapplied to the olefin wax composition and feedstock olefin waxcomposition embodiments having the olefin carbon number compositionsand/or the carbon number ranges and average olefin molecular weightranges as described herein.

The olefin wax composition comprises olefins and/or alpha olefins withcarbon number distributions, alpha olefin contents, molecular weightdistributions, and needle penetration values as described herein.

In one embodiment, the olefin wax composition or feedstock olefin waxcomposition comprises greater than 70 wt % olefins having from 20 to 24carbon atoms. In a further embodiment, the olefin wax compositioncomprises greater than 80 wt % olefins having from 20 to 24 carbonatoms. In still a further embodiment, the olefin wax compositioncomprises greater than 85 wt % percent olefins having from 20 to 24carbon atoms. In yet a further embodiment, the olefin wax compositioncomprises greater than 90 wt % olefins having from 20 to 24 carbonatoms. In still a further embodiment, the olefin wax compositioncomprises greater than 95 wt % olefins having from 20 to 24 carbonatoms.

In one embodiment, the olefin wax composition or feedstock olefin waxcomposition comprises greater than 50 wt % olefins having from 24 to 28carbon atoms. In a further embodiment, the olefin wax compositioncomprises greater than 60 wt % olefins having from 24 to 28 carbonatoms. In a further embodiment, the olefin wax composition comprisesgreater than 70 wt % olefins having from 24 to 28 carbon atoms. In yet afurther embodiment, the olefin wax composition comprises greater than 80wt % olefins having from 24 to 28 carbon atoms. In still a furtherembodiment, the olefin wax composition comprises greater than 90 wt %olefins having from 24 to 28 carbon atoms.

In one embodiment, the olefin wax composition or feedstock olefin waxcomposition comprises greater than 50 wt % olefins having from 26 to 28carbon atoms. In a further embodiment, the olefin wax compositioncomprises greater than 60 wt % olefins having from 26 to 28 carbonatoms. In a further embodiment, the olefin wax composition comprisesgreater than 70 wt % olefins having from 26 to 28 carbon atoms. In yet afurther embodiment, the olefin wax composition comprises greater than 80wt % olefins having from 26 to 28 carbon atoms. In still a furtherembodiment, the olefin wax composition comprises greater than 90 wt %olefins having from 26 to 28 carbon atoms.

In one embodiment, the olefin wax composition or feedstock olefin waxcomposition comprises greater than 70 wt % olefins having at least 30carbon atoms. In a further embodiment, the olefin wax compositioncomprises greater than 80 wt % olefins having at least 30 carbon atoms.In still a further embodiment, the olefin wax composition comprisesgreater than 85 wt % percent olefins having from at least 30 carbonatoms. In yet a further embodiment, the olefin wax composition comprisesgreater than 90 wt % olefins having at least 30 carbon atoms. In still afurther embodiment, the olefin wax composition comprises greater than 95wt % olefins having at least 30 carbon atoms.

Alternatively, the olefin wax composition or feedstock olefin waxcomposition may be described as an olefin wax composition having aparticular average molecular weight of the olefin components thereof. Insome embodiments, the olefin wax composition has an average olefinmolecular weight greater than 260 grams/mole. In yet another embodiment,the olefin wax composition has an average olefin molecular weightgreater than 330 grams/mole. In yet another embodiment, the olefin waxcomposition has an average olefin molecular weight greater than 400grams/mole. In other embodiments, the olefin wax composition has anaverage olefin molecular weight between 260 grams/mole and 340grams/mole; alternatively, between 280 grams/mole and 320 grams/mole;alternatively, between 290 grams/mole and 310 grams/mole. In anotherembodiment, the olefin wax composition has an average olefin molecularweight between 330 grams/mole and 420 grams/mole; alternatively, between350 grams/mole and 400 grams/mole; alternatively, between 360 grams/moleand 390 grams/mole. In yet another embodiment, the olefin waxcomposition has an average olefin molecular weight between 440grams/mole and 550 grams/mole; alternatively, between 460 grams/mole and530 grams/mole; alternatively, between 480 grams/mole and 510grams/mole.

Commercially available olefin waxes commonly contain a number of alphaolefins having at least about 20 carbon atoms, alpha olefins having atleast about 20 carbon atoms, as well as other compounds (smaller alphaolefins, smaller normal alpha olefins, internal olefins, vinylidene, orothers). For example, Alpha Olefin C₂₀₋₂₄ (Chevron Phillips ChemicalCompany LP, The Woodlands, Tex.) comprises from about 35-55 wt % C₂₀olefin, about 25-45 wt % C₂₂ olefin, about 10-26 wt % C₂₄ olefin, about3 wt % olefins smaller than C₂₀, and about 2 wt % olefins larger thanC₂₄. Alpha Olefin C₂₀₋₂₄ is an exemplary olefin wax within thedefinition “comprising an olefin having at least 20 carbon atoms” asused herein. The invention is not limited to this or any otherparticular commercially available olefin wax. Also, an olefin waxconsisting essentially of an olefin having 20 carbon atoms (or anotherolefin having a particular number of carbon atoms greater than 20) canalso be used in the present invention.

In one embodiment, the olefin wax composition comprises an olefin havingfrom about 20 carbon atoms to about 24 carbon atoms. In anotherembodiment, the olefin wax composition comprises an olefin having fromabout 26 carbon atoms to about 28 carbon atoms. In yet anotherembodiment the olefin wax composition comprises an olefin having fromabout 26 to about 28 carbon atoms. In an additional embodiment, theolefin wax composition comprises an olefin having at least 30 carbonatoms.

Commercially available olefin waxes may further comprise vinylidene orinternal olefins, up to as much as about 40-50 wt % of the wax. In oneembodiment, and regardless of the number of carbons in the olefin, theolefin wax is a high alpha (HA) AO wax. By “HA wax” is meant a waxcomprising (a) one or more alpha olefins and (b) less than about 20 wt %vinylidene or internal olefins.

Independently, commercially available olefin wax compositions mayfurther comprise non-olefin hydrocarbons, such as paraffins(hydrocarbons wherein all bonds between carbon atoms are single bonds).Other components known in the art to acceptably be present in olefinwaxes can be present as well. For example, some applicable olefin waxcompositions and/or feedstock olefin wax composition may containoxygenated components such as alcohols, aldehydes, and ketones, amongothers. Thus, oxygenated components may not impact the generallyobserved decrease in the needle penetration of the hardened olefin waxcompositions or the oxidized olefin wax compositions described herein.

Known olefin waxes include olefin streams from ethylene oligomerization,cracked heavy waxes (e.g. Fischer-Tropsch waxes), and mixtures ofparaffins and olefins, among others. Additionally, the olefin waxcompositions and/or the feedstock olefin wax compositions may includeFischer-Tropsch waxes comprising a mixture of paraffin waxes and olefinwaxes which meet the describe olefin wax composition and/or feedstockolefin wax compositions described herein. One source of commerciallyavailable Fischer-Tropsch waxes is Sasol, Johannesburg, South Africa.

In some embodiments, the olefin wax composition or feedstock olefin waxcomposition comprises commercially available normal alpha olefin waxes.In other embodiments, the olefin wax composition consists essentially ofcommercially available normal alpha olefin waxes. One source ofcommercially available alpha olefin waxes is Chevron Phillips ChemicalCompany LP, The Woodlands, Tex. The following are published physical andchemical characteristics of the normal alpha olefin waxes Alpha OlefinC₂₀₋₂₄, Alpha Olefin C₂₄₋₂₈, Alpha Olefin C₂₆₋₂₈, Alpha Olefin C₃₀₊, andAlpha Olefin C_(30+HA), which are provided for illustrative purposes asexemplary feedstock olefin waxes. The invention is not limited to theseparticular feedstock olefin waxes.

Typical Value (Typical Range) Characteristic C₂₀₋₂₄ C₂₄₋₂₈ C₂₆₋₂₈ C₃₀₊C_(30 + HA) Drop melt point, ° F. 96 (ASTM D 87) 143 (140-158) 125(122-130) 162 (154-174) 159 (150-164) (ASTM D 127) Oil content (MEK 3.7(3.0-5.1) 3.8 (3.2-5.3) 1.50 (1.0-2.0) 1.5 (1.2-3.0) extraction), wt. %Needle Penetration 150 59 (48-70) 48 (40-60) 13 (11-17) 15.5 (12-18)@77° F., dmm Needle Penetration 24 (18-30) 32 (24-44) @ 100° F., dmmNeedle Penetration 34 (25-50) 40 (30-56) @ 110° F., dmm Flash Point 362°F. (183° C.) 425° F. (218° C.) 417° F. (214° C.) 485° F. (252° C.) 432°F. (222° C.) (ASTM D 93) Saybolt Color 30 25 30 20+ 20+ KinematicViscosity 2.0 (1.8-2.2) 3.5 (3.2-4.0) 3.4 (3.2-3.6) 6.5 (5.0-10.0) 6.4(5.0-9.0) @ 100° C., cSt % Alpha olefins 86 (83-92) 54 (40-60) 79(70-82) 62 (50-65) 76 (70-81) (¹H-NMR) % Vinylidenes 8 (6-15) 30 (25-55)16 (11-17) 30 (25-45) 18 (15-25) (¹H-NMR) % Internal olefins 3 (2-5) 18(10-22) 3 (2-8) 10 (5-20) 5.3 (4-10) (¹H-NMR) Drop melt point, ° F. 96*154 125 164 150 (ASTM D 127) Oil content (MEK 4.60 5.00 1.50 1.5extraction), wt. % Needle Penetration 150 59 48 13 15.5 @ 77° F., dmmNeedle Penetration 24 32 @ 100° F., dmm Needle Penetration 34 40 @ 110°F., dmm Flash Point 362° F. (183° C.) 425° F. (218° C.) 417° F. (214°C.) 485° F. (252° C.) 432° F. (222° C.) (ASTM D 93) Saybolt Color 30 2530 20+ 20+

The following examples are included to demonstrate preferred embodimentsof the invention. It should be appreciated by those of skill in the artthat the techniques disclosed in the examples which follow representtechniques discovered by the inventors to function well in the practiceof the invention. However, those of skill in the art should, in light ofthe present disclosure, appreciate that many changes can be made in thespecific embodiments which are disclosed and still obtain a like orsimilar result without departing from the spirit and scope of theinvention.

Examples 1-8 relate to hardened olefin waxes.

Example 1

500 g of normal alpha olefin wax C30+ (Chevron Phillips Chemical CompanyLP) was placed into a four-neck flask, which was equipped with a heatingmantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to220° C. and the agitation was set at 400 rpm. A stream of air was thenintroduced below the wax liquid at 1 CFH. The reaction was maintained at220° C. for 30 min. The contents were allowed to cool to 100° C. andwere discharged. The resulting material appeared as a white solid.

Example Properties Control 1 Needle Penetration Number at 25° C., dmm 134 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <1 <1 AcidNumber, mg KOH/g (ASTM D 974) <1 <1 Melt Viscosity at 100° C., cSt (ASTMD 445) 7.3 8.3 Drop Melting Point, ° C. (ASTM D 127) 77 72

Example 2

500 g of normal alpha olefin wax C30+ (Chevron Phillips Chemical CompanyLP) was placed into a four-neck flask, which was equipped with a heatingmantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to220° C. and the agitation was set at 400 rpm. A stream of air was thenintroduced below the wax liquid at 1 CFH. The reaction was maintained at220° C. for 1 hour. The contents were allowed to cool to 100° C. andwere discharged. The resulting material appeared as a white solid.

Example Properties Control 2 Needle Penetration Number at 25° C., dmm 133 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 3.5 AcidNumber, mg KOH/g (ASTM D 974) <0.2 1.4 Melt Viscosity at 100° C., cSt(ASTM D 445) 7.3 10.5 Drop Melting Point, ° C. (ASTM D 127) 77 73

Example 3

500 g of normal alpha olefin wax C30+HA (Chevron Phillips ChemicalCompany LP) was placed into a four-neck flask, which was equipped with aheating mantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to220° C. and the agitation was set at 400 rpm. A stream of air was thenintroduced below the wax liquid at 1 CFH. The reaction was maintained at220° C. for 30 min. The contents were allowed to cool to 100° C. andwere discharged. The resulting material appeared as a white solid.

Example Properties Control 3 Needle Penetration Number at 25° C., dmm 146.5 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 0.7Acid Number, mg KOH/g (ASTM D 974) <0.2 1.0 Melt Viscosity at 100° C.,cSt (ASTM D 445) 7 11 Drop Melting Point, ° C. (ASTM D 127) 71 70

Example 4

500 g of normal alpha olefin wax C26/28 (Chevron Phillips ChemicalCompany LP) was placed into a four-neck flask, which was equipped with aheating mantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to220° C. and the agitation was set at 400 rpm. A stream of air was thenintroduced below the wax liquid at 1 CFH. The reaction was maintained at220° C. for 15 min. The contents were allowed to cool to 100° C. andwere discharged. The resulting material appeared as a white solid.

Example Properties Control 4 Needle Penetration Number at 25° C., dmm 4523 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 <0.5Acid Number, mg KOH/g (ASTM D 974) <0.2 <0.2 Melt Viscosity at 100° C.,cSt (ASTM D 445) 3.4 4 Drop Melting Point, ° C. (ASTM D 127) 52 52

Example 5

500 g of normal alpha olefin wax C30+ (Chevron Phillips Chemical CompanyLP) was placed into a four-neck flask, which was equipped with a heatingmantle, a thermocouple, a single blade agitator, and a side armconnected to a receiving flask. The wax was heated to 220° C. and theagitation was set at 100 rpm. A stream of air was then introduced abovethe surface of wax liquid at 4 CFH. The reaction was maintained at 220°C. for 3 hour. The contents were allowed to cool to 100° C. and weredischarged. The resulting material appeared as a white solid.

Example Properties Control 5 Needle Penetration Number at 25° C., dmm 134 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 <0.5Acid Number, mg KOH/g (ASTM D 974) <0.2 <0.2 Melt Viscosity at 100° C.,cSt (ASTM D 445) 7.3 11.9 Drop Melting Point, ° C. (ASTM D 127) 77 74

Example 6

500 g of normal alpha olefin wax C30+HA (Chevron Phillips ChemicalCompany LP) was placed into a four-neck flask, which was equipped with aheating mantle, a thermocouple, a single blade agitator, and a side armconnected to a receiving flask. The wax was heated to 220° C. and theagitation was set at 100 rpm. A stream of air was then introduced abovethe surface of wax liquid at 4 cubic feet per hour. The reaction wasmaintained at 220° C. for 4 hour. The contents were allowed to cool to100° C. and were discharged. The resulting material appeared as a whitesolid.

Example Properties Control 6 Needle Penetration Number at 25° C., dmm 145 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 <0.5Acid Number, mg KOH/g (ASTM D 974) <0.2 0.3 Melt Viscosity at 100° C.,cSt (ASTM D 445) 7 13.7 Drop Melting Point, ° C. (ASTM D 127) 71 69

Example 7

200 g of normal alpha olefin wax C30+ (Chevron Phillips Chemical CompanyLP) in a 500 ml beaker was placed in an oven (Constant Temperature Oven,Model D-K 63, Baxter) with oven-temperature set at 120° C. The waxcontents were allowed to stay in the oven for 20 days in the presence ofair. The contents were allowed to cool to 100° C. and were discharged.The resulting material appeared as a white solid.

Example Properties Control 7 Needle Penetration Number at 25° C., dmm 134 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 3.0 AcidNumber, mg KOH/g (ASTM D 974) <0.2 2.5 Melt Viscosity at 100° C., cSt(ASTM D 445) 7.3 10.6 Drop Melting Point, ° C. (ASTM D 127) 77 75

Example 8

200 g of normal alpha olefin wax C30+HA (Chevron Phillips ChemicalCompany LP) in a 500 ml beaker was placed in an oven (ConstantTemperature Oven, Model D-K 63, Baxter) with oven-temperature set at120° C. The wax contents were allowed to stay in the oven for 20 days inthe presence of air. The contents were allowed to cool to 100° C. andwere discharged. The resulting material appeared as a white solid.

Example Properties Control 8 Needle Penetration Number at 25° C., dmm 146 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 <0.5Acid Number, mg KOH/g (ASTM D 974) <0.2 1.8 Melt Viscosity at 100° C.,cSt (ASTM D 445) 7 10.7 Drop Melting Point, ° C. (ASTM D 127) 71 69

Examples 1-8 report the unexpected result that hardened AO waxes withrelatively low viscosity can be produced by treatments that are eitherrelatively high temperature and short duration (Examples 1-6) orrelatively low temperature, very long duration, and very low air flowrate (contact with a headspace of air) (Examples 7-8).

Examples 9-16 relate to oxidized olefin waxes.

Example 9

500 g of normal alpha olefin wax C30+ (Chevron Phillips Chemical CompanyLP) was placed into a four-neck flask, which was equipped with a heatingmantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to130° C. and the agitation was set at 400 rpm. Then a steady stream ofair was introduced at 1.7 CFH. The reaction was maintained at 130° C.for 24 hours. The contents were allowed to cool to 100° C. and weredischarged. The resulting material appeared as a white to light yellowsolid.

Example Properties Control 9 Needle Penetration Number at 25° C., dmm 136 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <1 45 AcidNumber, mg KOH/g (ASTM D 974) <1 15 Melt Viscosity at 100° C., cSt (ASTMD 445) 7.3 16.6 Drop Melting Point, ° C. (ASTM D 127) 77 74

Example 10

500 g of normal alpha olefin wax C30+HA (Chevron Phillips ChemicalCompany LP) was placed into a four-neck flask, which was equipped with aheating mantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to130° C. and the agitation was set at 400 rpm. Then a steady stream ofair was introduced at 1.7 CFH. The reaction was maintained at 130° C.for 24 hours. The contents were allowed to cool to 100° C. and weredischarged. The resulting material appeared as a white to light yellowsolid.

Example Properties Control 10 Needle Penetration Number at 25° C., dmm14 13 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 50Acid Number, mg KOH/g (ASTM D 974) <0.2 17 Melt Viscosity at 100° C.,cSt (ASTM D 445) 7 13.3 Drop Melting Point, ° C. (ASTM D 127) 71 71

Example 11

500 g of normal alpha olefin wax C30+ (Chevron Phillips Chemical CompanyLP) was placed into a four-neck flask, which was equipped with a heatingmantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to145° C. and the agitation was set at 400 rpm. Then a steady stream ofair was introduced at 3.4 CFH. The reaction was maintained at 145° C.for 8 hours. The contents were allowed to cool to 100° C. and weredischarged. The resulting material appeared as a white solid.

Example Properties Control 11 Needle Penetration Number at 25° C., dmm13 12 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 97Acid Number, mg KOH/g (ASTM D 974) <0.2 37 Melt Viscosity at 100° C.,cSt (ASTM D 445) 7.3 25 Drop Melting Point, ° C. (ASTM D 127) 77 74

Example 12

500 g of normal alpha olefin wax C30+HA (Chevron Phillips ChemicalCompany LP) was placed into a four-neck flask, which was equipped with aheating mantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to145° C. and the agitation was set at 400 rpm. Then a steady stream ofair was introduced at 3.4 CFH. The reaction was maintained at 145° C.for 8 hours. The contents were allowed to cool to 100° C. and weredischarged. The resulting material appeared as a white solid.

Example Properties Control 12 Needle Penetration Number at 25° C., dmm14 14 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 68Acid Number, mg KOH/g (ASTM D 974) <0.2 28 Melt Viscosity at 100° C.,cSt (ASTM D 445) 7 22.8 Drop Melting Point, ° C. (ASTM D 127) 71 70

Example 13

500 g of normal alpha olefin wax C26/28 (Chevron Phillips ChemicalCompany LP) was placed into a four-neck flask, which was equipped with aheating mantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to145° C. and the agitation was set at 400 rpm. Then a steady stream ofair was introduced at 3.4 CFH. The reaction was maintained at 145° C.for 8 hours. The contents were allowed to cool to 100° C. and weredischarged. The resulting material appeared as a white solid.

Example Properties Control 13 Needle Penetration Number at 25° C., dmm45 33 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 91Acid Number, mg KOH/g (ASTM D 974) <0.2 40 Melt Viscosity at 100° C.,cSt (ASTM D 445) 3.4 15.5 Drop Melting Point, ° C. (ASTM D 127) 51 60

Example 14

500 g of normal alpha olefin wax C30+ (Chevron Phillips Chemical CompanyLP) was placed into a four-neck flask, which was equipped with a heatingmantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to145° C. and the agitation was set at 400 rpm. Then a steady stream ofair was introduced at 3.4 CFH. The reaction was maintained at 145° C.for 24 hours. The contents were allowed to cool to 100° C. and weredischarged. The resulting material appeared as a yellow solid.

Example Properties Control 14 Needle Penetration Number at 25° C., dmm13 20 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 150Acid Number, mg KOH/g (ASTM D 974) <0.2 46 Melt Viscosity at 100° C.,cSt (ASTM D 445) 7.3 70.5 Drop Melting Point, ° C. (ASTM D 127) 77 70

Example 15

500 g of normal alpha olefin wax C30+HA (Chevron Phillips ChemicalCompany LP) was placed into a four-neck flask, which was equipped with aheating mantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to145° C. and the agitation was set at 400 rpm. Then a steady stream ofair was introduced at 3.4 CFH. The reaction was maintained at 145° C.for 24 hours. The contents were allowed to cool to 100° C. and weredischarged. The resulting material appeared as a white solid.

Example Properties Control 15 Needle Penetration Number at 25° C., dmm14 14 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 136Acid Number, mg KOH/g (ASTM D 974) <0.2 44 Melt Viscosity at 100° C.,cSt (ASTM D 445) 7 65.9 Drop Melting Point, ° C. (ASTM D 127) 71 68

Example 16

500 g of normal alpha olefin wax C26/28 (Chevron Phillips ChemicalCompany LP) was placed into a four-neck flask, which was equipped with aheating mantle, a thermocouple, a single blade agitator, an air sparger(cylindrical, 1″ in length and ⅜″ in diameter, average pore size 15 μm),and a side arm connected to a receiving flask. The wax was heated to145° C. and the agitation was set at 400 rpm. Then a steady stream ofair was introduced at 3.4 CFH. The reaction was maintained at 145° C.for 24 hours. The contents were allowed to cool to 100° C. and weredischarged. The resulting material appeared as a white solid.

Example Properties Control 16 Needle Penetration Number at 25° C., dmm45 55 (ASTM D1321) Saponification Number, mg KOH/g (ASTM D 94) <0.5 177Acid Number, mg KOH/g (ASTM D 974) <0.2 40 Melt Viscosity at 100° C.,cSt (ASTM D 445) 3.4 56.3 Drop Melting Point, ° C. (ASTM D 127) 51 55

Examples 17-20

Mixtures of an alpha olefin wax and an additive, having the proportionsindicated in the table below, were each placed in an oven andoccasionally agitated to obtain a clear solution. The samples wereallowed to cool to room temperature to provide a solid wax mixture. Thesamples were then tested for needle penetration and drop melt point.Needle penetrations, at 25° C., for the mixtures were measured usingASTM D1321. Drop melt points for the mixtures were measured using ASTM D127.

Needle Drop Melt Wax Additive Penetration Point Example (wt. %) (wt. %)(dmm) (° C.) 17 CPChem Alpha Olefin — 16.5 dmm 71 (Control) 30 + HA (100wt. %) 18 CPChem Alpha Olefin Stearic Acid 21.5 dmm 71 30 + HA (90 wt.%) (10 wt. %) 19 CPChem Alpha Olefin Polyanhydride 24-28 23.5 dmm 6930 + HA (90 wt. %) (10 wt. %) 20 CPChem Alpha OlefinEthylene-bis-stearamide  10 dmm >100 30 + HA (90 wt. %) (10 wt. %)

Example 21-26

Mixtures of an alpha olefin wax and ethylene-bis-stearamide (EBSA, 98%,from Aldrich), having the proportions indicated in the table below, wereeach placed in a beaker and heated in an oven at 140° C. A clearsolution was obtained in half hour from occasional agitation with astirring rod. The samples were allowed to cool to room temperaturegiving a white solid. The samples were then tested for needlepenetration and kinematic viscosity. Needle penetrations, at 25° C., forthe mixtures were measured using ASTM D 1321. Kinematic viscosities forthe mixtures were measured using ASTM D 445.

Ethylene-bis- Needle Viscosity Example Wax (wt. %) stearamidePenetration (Temperature) 21 CPChem Alpha Olefin 26-28 — 44 dmm 3.5(100° C.) (Control) (100 wt. %) 22 CPChem Alpha Olefin 26-28 2 wt. % 32dmm 2.2 (140° C.) (98 wt. %) 23 CPChem Alpha Olefin 26-28 5 wt. % 30 dmm2.3 (140° C.) (95 wt. %) 24 CPChem Alpha Olefin 30+ — 14 dmm 7.0 (100°C.) (Control) (100 wt. %) 25 CPChem Alpha Olefin 30+ 2 wt. % 12 dmm 4.2(140° C.) (98 wt. %) 26 CPChem Alpha Olefin 30+ 5 wt. % 12 dmm 4.1 (140°C.) (95 wt. %)

Example 27

Mixtures of alpha olefin waxes and ethylene-bis-stearamide, having thecompositions indicated in the table below, were prepared using a similarprocedure as used in Examples 21-26. The samples were then tested forneedle penetration and drop melt point. Needle penetrations, at 25° C.,for the mixtures were measured using ASTM D1321. Drop melt points forthe mixtures were measured using ASTM D 127.

CPChem Alpha CPChem Alpha CPChem Alpha CPChem Alpha Olefin 20-24 Olefin26-28 Olefin 30+ HA Olefin 30 + Ethylene- Drop Drop Drop Drop Bis-Needle Melt Needle Melt Needle Melt Needle Melt Stearamide PenetrationPoint Penetration Point Penetration Point Penetration Point (wt. %)(dmm) (° C.) (dmm) (° C.) (dmm) (° C.) (dmm) (° C.) 0 wt. % 160.5 35.648.5 50.6 16.5 70.6 12 77.2 (Control) 1 108 66 34.5 97 11.5 99 8.5 99 291 78 28.5 99 12.5 107 6 102 5 81.5 78 26.5 110 9.5 114 — 113 10 85 11129.5 117 10 121 5.5 120

All of the compositions and methods disclosed and claimed herein can bemade and executed without undue experimentation in light of the presentdisclosure. While the compositions and methods of this invention havebeen described in terms of particular embodiments, it will be apparentto those of skill in the art that variations may be applied to thecompositions and methods and in the steps or in the sequence of steps ofthe methods described herein without departing from the concept, spiritand scope of the invention as defined by the appended claims.

1. A hardened olefin wax composition produced from a feedstock olefinwax composition by contacting the feedstock olefin wax composition withan oxygen-containing gas at a temperature greater than a melting pointof the feedstock olefin wax composition, the hardened olefin waxcomposition having: a needle penetration value at 25° C. at least 5percent less than a needle penetration value at 25° C. of the feedstockolefin wax composition; a kinematic viscosity at 100° C. of up to about200% greater than the kinematic viscosity of the feedstock olefin waxcomposition; and a saphonification number less than 5 mg KOH/g hardenedolefin wax composition.
 2. The hardened olefin wax composition of claim1, wherein the feedstock olefin wax is an alpha olefin wax.
 3. Thehardened olefin wax composition of claim 2, wherein the alpha olefin waxhas an average olefin molecular weight between 260 grams/mole and 340grams/mole, and the hardened olefin wax composition has a needlepenetration at 25° C. less than 100 dmm.
 4. The hardened olefin waxcomposition of claim 3, having an acid number less than 12 mg KOH/ghardened olefin wax composition.
 5. A hardened olefin wax composition ofclaim 2, wherein the alpha olefin wax has an average olefin molecularweight between 330 and 420 grams/mole, and the hardened olefin waxcomposition has a needle penetration at 25° C. less than 35 dmm.
 6. Thehardened olefin wax composition of claim 5, having a kinematic viscosityat 100° C. between 3 cSt and 15 cSt.
 7. The hardened olefin waxcomposition of claim 5, having an acid number less than 12 mg KOH/g. 8.The hardened olefin wax composition of claim 5, having a kinematicviscosity at 100° C. between 3 cSt and 15 cSt and having an acid numberless than 12 mg KOH/g hardened olefin wax composition.
 9. The hardenedolefin wax composition of claim 2, wherein the alpha olefin wax has anaverage olefin molecular weight between 440 grams/mole and 550grams/mole, and the hardened olefin wax composition has a needlepenetration at 25° C. less than 10 dmm.
 10. The hardened olefin waxcomposition of claim 9, having kinematic viscosity at 100° C. between 7cSt and 35 cSt.
 11. The hardened olefin wax composition of claim 9,having an acid number less than 12 mg KOH/g hardened olefin waxcomposition.
 12. The hardened olefin wax composition of claim 9, havingkinematic viscosity at 100° C. between 7 cSt and 35 cSt and having anacid number less than 12 mg KOH/g hardened olefin wax composition.
 13. Aprocess to produce a hardened olefin wax composition, comprising:contacting a feedstock olefin wax composition with an oxygen-containinggas at a temperature greater than a melting point of the feedstockolefin wax composition, to produce a hardened olefin wax composition,wherein the hardened olefin wax composition has a needle penetrationvalue at 25° C. at least 5 percent less than a needle penetration valueat 25° C. of the feedstock olefin wax composition, the hardened olefinwax composition has a kinematic viscosity at 100° C. up to about 200%greater than the kinematic viscosity of the feedstock olefin waxcomposition, and the hardened olefin wax composition has asaphonification number less than 5 mg KOH/g hardened olefin waxcomposition.
 14. The process of claim 13, wherein the feedstock olefinwax is an alpha olefin wax.
 15. The process of claim 13, wherein thefeedstock olefin wax composition and the oxygen-containing gas arecontacted at a temperature between the melting point of the feedstockolefin wax composition and 300° C.
 16. The process of claim 13, whereinthe oxygen-containing gas is selected from the group consisting of pureoxygen, oxygen diluted with an inert gas, air, and air diluted with aninert gas.
 17. The process of claim 16, wherein the contacting stepcomprises contacting air with the feedstock olefin wax at an air flowless than 0.1 cubic feet/hour/kg feedstock olefin wax composition andwithout substantial agitation of the feedstock olefin wax composition.18. The process of claim 17, wherein the contacting step has a durationgreater than 1 day.
 19. The process of claim 16, wherein the contactingstep comprises contacting air with the feedstock olefin wax at an airflow is between 0.1 cubic feet/hour/kg feedstock olefin wax compositionand 15 cubic feet/hour/kg feedstock olefin wax composition.
 20. Theprocess of claim 19, wherein the contacting step has a duration isbetween 1 minute and 12 hours.